CN110205087A - Heat cure no-solvent type organosilicon conductive adhesive - Google Patents
Heat cure no-solvent type organosilicon conductive adhesive Download PDFInfo
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- CN110205087A CN110205087A CN201910501418.3A CN201910501418A CN110205087A CN 110205087 A CN110205087 A CN 110205087A CN 201910501418 A CN201910501418 A CN 201910501418A CN 110205087 A CN110205087 A CN 110205087A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/085—Copper
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Abstract
The invention discloses a kind of heat cure no-solvent type organosilicon conductive adhesives, belong to conductive adhesive preparation field.Based on parts by weight, which includes the dimethyl silicone polymer of 10 ~ 40 parts of (methyl) acryloxyalkyl lists sealing end, 50 ~ 80 parts of conductive powder bodies, 0.5-5 parts of free radical thermal initiators, 1 ~ 10 part of fumed silica.Compared with additional organosilicon conducting resinl, free radical cure silicone conducting resinl of the invention will not generate the platinum catalyst intoxicating phenomenon of similar additional organosilicon, have good adhesive force to various substrates, can be solidified in a low temperature of 80 degree.
Description
Technical field
The invention belongs to conductive adhesive preparation fields, and in particular to a kind of heat-setting no-solvent type organosilicon is conductive
Glue.
Background technique
Conductive adhesive is widely used in microelectronics assembly, solar energy imbrication conductive adhesive, and crystal resonator wafer conduction is glued
It connects, the purposes such as substitution of scolding tin.Conducting resinl is mainly by resin matrix, conducting particles and dispersing additive, the composition such as auxiliary agent.Resin
Matrix mainly has epoxy resin, acrylate, organosilicon, the materials such as polyurethane.Wherein organosilicon conductive adhesive is because heat-resisting
Temperature is high, and low temperature flexibility is good, ultraviolet-resistant aging, and anti-high and low-temp impact, high wet performance resistant to high temperatures is outstanding, develops in recent years fast
Speed.
The main wetly solidification of the curing mode of single-component organic silicon conducting resinl and Si―H addition reaction type are heating and curing, and compare
In condensed type moisture-curable organosilicon, the curing rate that add-on type is heating and curing is fast, production efficiency can be greatly improved, in microelectronics
It is used widely in the fields such as assembly electronic component encapsulation solar energy imbrication.Additional organosilicon conducting resinl is usually used
Vinyl silicone oil or vinyl MQ resin, containing hydrogen silicone oil, conductive powder body, platinum catalyst and inhibitor are prepared as a raw material, and are added
Inhibitor dissociation or volatilization produce active platinum initiation hydrosilylation when hot.But hydrosilylation is wanted to by bonding material
Ask harsh, if glued material surface attachment is organic phosphorus, sulphur, amine, organotin be frequently can lead in the case where the substances such as moisture
Platinum catalyst is poisoned and occurs solidifying bad.Additional organosilicon conducting resinl is also more harsh to the selection of conductive powder body, surface
Inorganic agent poisons platinum catalyst often also to influence the solidification of conducting resinl.Additional organosilicon is not also as molecular structure has pole
Property, all without adhesive force, needs to reach by adhesion promoter certain adhesive strength, however to most of material
Its adhesive strength is also more much smaller than condensed type organic silicon, and most of adhesion promoters only reach 120 degree or more of high temperature
Adhesive force can be just generated when solidification, therefore one-component additional organosilicon is difficult to accomplish 80 degree of low-temperature settings below, Wu Faying
To the conductive adhesive purposes of thermo-labile material.
Summary of the invention
The object of the present invention is to provide a kind of heat-setting no-solvent type organosilicon conductive adhesives.
Realizing the technical solution of the object of the invention is: a kind of heat-setting no-solvent type organosilicon conductive adhesive, with
Parts by weight meter, the dimethyl silicone polymer including 10~40 parts of (methyl) acryloxyalkyl lists sealing end, 50~80 parts are led
Electric powder, 0.5-5 parts of free radical thermal initiators, 1~10 part of fumed silica.
Further, the dimethyl silicone polymer of (methyl) acryloxyalkyl list sealing end of the present invention is (referred to as
Single sealing end (methyl) acryloyl propyl group organosilicon), structure is as follows:
Wherein,
R1For H or methyl;
R2For CH2Or CH2CH2CH2;
R3For methyl, methoxyl group is or, ethyoxyl or isopropoxy;
R4For methyl, methoxyl group is or, ethyoxyl or isopropoxy;
The integer that n is 200~2000.
Further, conductive powder body of the present invention is silver powder, silver-coated copper powder, nickel powder, carbon dust etc..
Further, free radical thermal initiator of the present invention is azo or organic peroxide, and azo is preferred
AIBN, AIBME, the preferred lauroyl peroxide of organic peroxide, benzoyl peroxide, peroxidized t-butyl perbenzoate.
Further, the preferred AEROSIL hydrophobic silica R972 of fumed silica of the invention.
The preparation method of the dimethyl silicone polymer of (methyl) acryloxyalkyl list sealing end of the invention, step
Be: 1.0~10 parts by weight of silane coupling agent and 100 parts by weight of hydroxy silicon oil containing (methyl) acryloxy are in catalytic reaction
It under the action of agent, reacts at 80 ± 5 DEG C, reaches addition 1.0~10 weight of hexamethyldisilazane after certain viscosity
Part removes the remaining hydroxyl of the other end, obtains the monofunctional dimethyl silicone polymer that one end is (methyl) acryloxy,
Monoblocking reaction organosilicon i.e. of the present invention.
In preparation method, addition hexamethyldisilazane removes the remaining hydroxyl of the other end after reaching certain viscosity, should
Certain viscosity is different and different according to raw material initial viscosity, and usually 1.2~1.8 times of initial feed hydroxy silicon oil viscosity are
Preferably.
In preparation method, the structure of hydroxy silicon oil is as follows:
The integer that n is 80~800.
Viscosity is 100mPas~10000mPas.
In preparation method, contain the silane coupling agent of (methyl) acryloxy are as follows: γ-methacryloxypropyl three
Methoxy silane, γ-methacryloxypropylmethyl dimethoxysilane, three ethoxy of γ-methacryloxypropyl
Base silane, three isopropoxy silane of γ-methacryloxypropyl, γ-acryloyloxypropyltrimethoxysilane, γ-
Acryloxypropyl dimethoxysilane, γ-acryloxypropyl triethoxysilane, γ-acryloxy third
Three isopropoxy silane of base, γ-methacryloxymethyl trimethoxy silane, γ-methacryloxymethyl methyl
Dimethoxysilane, γ-methacryloxymethyl triethoxysilane, three isopropyl oxygen of γ-methacryloxymethyl
Base silane, γ-acryloyloxymethyl trimethoxy silane, γ-acryloyloxymethyl methyl dimethoxysilane, γ-the third
Alkene pivaloyloxymethyl triethoxysilane, the mixing of one or more of three isopropoxy silane of γ-acryloyloxymethyl etc..
In preparation method, catalysts are as follows: organo-tin compound, bismuth organic compound, titanate ester compound, Louis
The mixing of one or more of this acids or Louis's alkaloid compound.
Compared with prior art, the invention has the advantages that the conducting resinl has the advantages of organosilicon wet-heat resisting high-low temperature resistant,
To the good adhesive force of various substrates, solidfied material elongation is high, and flexibility is good, can solidify in a low temperature of 80 degree, but not
Generate the platinum catalyst intoxicating phenomenon of similar additional organosilicon.
Specific embodiment
It is illustrated below with reference to specific example.
Free radical thermal initiator of the present invention is azo or organic peroxide, wherein
Azo initiator refers to that the radical initiator containing nitrogen nitrogen double bond in molecule structure, general general formula are R-N
=N-R, wherein R-N key is weak bond, is easily broken off to form free radical, decomposition temperature is related with alkyl structure.If both ends are pair
Claim polarized substituent group in alkyl structure or alkyl (such as-CN ,-COOH ,-COOR etc.), then decomposition temperature declines.Azo
The decomposition almost all of initiator is first order reaction, a kind of free radical is only formed, without side reaction.Azo initiator property is steady
It is fixed, convenient for storage and transport.Oil-soluble azo-initiator has azodiisobutyronitrile (AIBN), azobisisoheptonitrile (ABVN)
Deng.But this kind of initiator contains cyano, there is certain toxicity.The oil-soluble azo for having been developed for not cyano-containing in recent years draws
Agent is sent out, such as azo-bis-iso-dimethyl (AIBME).The present invention preferred AIBN, AIBME.
The principal item of organic peroxide has hydroperoxides (ROOH), dialkyl peroxide (ROOR), diacyl
Peroxide (RCOOOOCR), peroxy esters (RCOOOR), peroxycarbonates (ROCOOOOCOR) and ketone peroxide [R2C
(OOH)2] etc..Benzoyl peroxide (BPO) is most common organic peroxide, is grain crystalline solid, normal to improve safety
Being commonly incorporated into 25% water becomes wet product, to reduce flammable and vibration sensitivity.In addition there is the peroxide of 50% plasticizer of concentration
Change benzoyl.Peroxide esters activity is higher and common peroxide.Such as the new enanthic acid 1 of peroxidating, 1- dimethyl -3- hydroxyl fourth
Ester, cumyl peroxyneodecanoate, the peroxides esters such as peroxidating neodecanoic acid tert-pentyl ester and t-butylperoxy pivarate are most
The compound of reactivity, all these peroxide esters are both needed to cryogenic freezing storage.Peroxide esters such as excessively sad tert-pentyl ester and mistake
Octanoic acid ter-butyl ester reactivity is slightly lower, can refrigerated storage.Benzylhydroperoxide tert-pentyl ester and this kind of peroxy esters of t-butyl perbenzoate are anti-
Answer activity minimum, thermostabilization is best, temperature can store at normal temperature.The preferred lauroyl peroxide of the present invention, benzoyl peroxide,
Peroxidized t-butyl perbenzoate.
Fumed silica (country is commonly called as fume colloidal silica) of the invention is using halosilanes through oxyhydrogen flame high-temperature water
A kind of solution amorphous silica product obtained, between 7~40nm, specific surface area generally exists the primary partial size of the product
100m2/ g~400m2It is a kind of extremely important inorganic nanometer powder material in/g range.Due to its superior stability, mend
Epistasis, thickening property and thixotropy and in rubber, plastics, electronics, coating, the fields such as adhesive are used widely.Organosilicon material
Expect that intensity itself is not high, and fumed silica is optimal reinforced filling.The preferred AEROSIL of fumed silica of the invention
(Germany wins wound) hydrophobic silica R972.
The present invention preferably singly blocks (methyl) acryloyl propyl group organosilicon rather than (methyl) acryloyl group of bi-end-blocking
Propyl organosilicon is can to prepare flexibility because can form combed macromolecular structure after single blocking silicone solidification
More preferably, the higher conducting resinl of elongation.The organosilicon crosslinked density of bi-end-blocking is big, it is difficult to prepare high drawing soft high flexibility
Conducting resinl.
One, the dimethyl silicone polymer of (methyl) acryloxyalkyl is synthesized
Viscosity is 100 parts of hydroxy silicon oil of 1000mPa.s by [synthesis -1 of single blocking silicone oligomer], metering system
4 parts of acryloxypropylethoxysilane trimethoxy silane, 0.05 part of dibutyl tin dilaurate is added to N2The cooling for reflux of protection fills
It is below 80 degree with oil bath heating to pot temperature inside the three-necked flask set, every 10 minutes test reaction fluid viscosities, one
Denier viscosity reaches 1500mPas and adds 2 parts of hexamethyldisilazane at once, continues heating reaction 1h and completely disappears to residual hydroxyl
(FTIR confirms no hydroxyl peak), end of reaction is evaporated under reduced pressure the small molecule alcohol reactant for taking off generation, and obtaining viscosity is
The single end of 1480mPas is the dimethyl silicone polymer of methacryloxy.Referred to as single-ended oligomer -1.
Viscosity is 100 parts of hydroxy silicon oil of 2000mPa.s by [synthesis -2 of single blocking silicone oligomer], acryloyl-oxy
4 parts of base propyl trimethoxy silicane, 0.1 part of Bismuth Octoate is added to N2In the three-necked flask of the cooling and reflux device of protection
Face is below 80 degree with oil bath heating to pot temperature, every 10 minutes test reaction fluid viscosities, once viscosity reaches
2800mPas adds 2.5 parts of hexamethyldisilazane at once, continues heating reaction 1h and completely disappears (FTIR confirmation to residual hydroxyl
There is no hydroxyl peak), end of reaction is evaporated under reduced pressure the small molecule alcohol reactant for taking off generation, and finally obtaining viscosity is 2810mPas
Single end be acryloxypropyl dimethyl silicone polymer.Referred to as single-ended oligomer -2.
Viscosity is 100 parts of hydroxy silicon oil of 5000mPa.s by [synthesis -3 of single blocking silicone oligomer], metering system
3.5 parts of pivaloyloxymethyl trimethoxy silane, 0.2 part of tin dilaurate dioctyl tin is added to N2The cooling for reflux of protection fills
It is below 80 degree with oil bath heating to pot temperature inside the three-necked flask set, every 10 minutes test reaction fluid viscosities, one
Denier viscosity reaches 7500mPas and adds 1.5 parts of hexamethyldisilazane at once, continues heating reaction 1h and disappears completely to residual hydroxyl
(FTIR confirms no hydroxyl peak) is lost, end of reaction is evaporated under reduced pressure the small molecule alcohol reactant for taking off generation, finally obtains viscous
It is the dimethyl silicone polymer of methacryloxypropyl that degree, which is the single end of 7715mPas,.Referred to as single-ended oligomer -3.
Viscosity is 100 parts of hydroxy silicon oil of 5000mPa.s by [synthesis -4 of single blocking silicone oligomer], metering system
3.5 parts of pivaloyloxymethyl triethoxysilane, 0.1 part of DBU lewis base is added to N2The cooling and reflux device of protection
It is below 80 degree with oil bath heating to pot temperature inside three-necked flask, every 10 minutes test reaction fluid viscosities, once it is viscous
Degree reaches 7500mPas and adds 2 parts of hexamethyldisilazane at once, continues heating reaction 1h to residual hydroxyl and completely disappears (FTIR
Confirm no hydroxyl peak), end of reaction is evaporated under reduced pressure the small molecule alcohol reactant for taking off generation, and finally obtaining viscosity is
The single end of 116mPas is the dimethyl silicone polymer of methacryloxypropyl.Referred to as single-ended oligomer -4.
Viscosity is 100 parts of hydroxy silicon oil of 1000mPa.s by [synthesis -1 of bi-end-blocking silicone oligomer], metering system
4 parts of acryloxypropylethoxysilane trimethoxy silane, 0.05 part of dibutyl tin dilaurate is added to N2The cooling for reflux of protection fills
It is below 80 degree with oil bath heating to pot temperature inside the three-necked flask set, every 10 minutes test reaction fluid viscosities, one
Denier viscosity reaches 2500mPas and stops heating.End of reaction is evaporated under reduced pressure the small molecule alcohol reactant for taking off generation, is glued
It is the dimethyl silicone polymer of methacryloxypropyl that degree, which is the both-end end of 2550mPas,.Abbreviation two-ended oligomer -1.
Two, conductive glue formula and its performance test
[embodiment 1]
By 15 parts of organosilicon of [synthesis -1 of single blocking silicone oligomer] preparation, 75 parts of flake silver powder, azo two is different
2.0 parts of butyronitrile, 10 parts of R972 fumed silica are added to planetary mixer, are stirred under vacuum upper three rollers grinding after being uniformly mixed
Machine carries out grinding three times, is then stirred under vacuum deaeration 30min with planetary mixer again, obtains organosilicon conductive adhesive, test it
The volume resistance of solidfied material, hardness and the following subordinate list of elongation:
Embodiment -1 | Embodiment -2 | Embodiment -3 | Embodiment -4 | Embodiment -5 | Embodiment -6 | Embodiment -7 | Embodiment -8 | Comparative example -1 | Comparative example -2 | |
Single-ended oligomer -1 | 15 | 15 | 15 | |||||||
Single-ended oligomer -2 | 17 | 17 | 17 | |||||||
Single-ended oligomer -3 | 20 | |||||||||
Single-ended oligomer -4 | 20 | |||||||||
Two-ended oligomer -1 | 15 | 15 | ||||||||
Flake silver powder | 75 | 75 | 75 | 75 | 75 | 75 | 75 | 75 | ||
Silver-coated copper powder | 75 | 75 | ||||||||
Azodiisobutyronitrile | 2 | |||||||||
Lauroyl peroxide | 2 | |||||||||
Benzoyl peroxide | 2 | 2 | 2 | 2 | 2 | 2 | 2 | |||
Peroxidized t-butyl perbenzoate | 2 | |||||||||
Fumed silica R972 | 10 | 10 | 10 | 8 | 8 | 8 | 5 | 5 | 10 | 10 |
It is total | 102 | 102 | 102 | 102 | 102 | 102 | 102 | 102 | 102 | 102 |
Condition of cure | 80 degree of 1h | 80 degree of 1h | 100 degree of 1h | 100 degree of 1h | 100 degree of 1h | 150 degree of 0.5h | 100 degree of 1h | 100 degree of 1h | 100 degree of 1h | 100 degree of 1h |
Volume resistance Ω .cm | 3.1*10-3 | 4.2*10-3 | 1.5*10-3 | 3.8*10-3 | 7.9*10-3 | 2.7*10-3 | 4.9*10-3 | 4.4*10-3 | 1.4*10-3 | 8.9*10-3 |
Hardness | A56 | A58 | A53 | A59 | A59 | A64 | A46 | A45 | A69 | A72 |
Elongation | 95% | 101% | 98% | 145% | 149% | 182% | 228% | 245% | 18% | 15% |
Embodiment 2~8 and comparative example 1~2, which are all made of, prepares corresponding conducting resinl simultaneously with the identical method of embodiment 1
It is as shown above to test its performance.
Find that the hardness of bi-end-blocking organosilicon conductive adhesive is larger, and elongation is substantially by comparing embodiment 3 and comparative example 1
Cripetura is spent, the conductive adhesive purposes having higher requirements to elongation is unsuitable for.And single blocking silicone has good electric conductivity
With higher elongation.
Although the embodiment of the present invention 1~8 only lists the monoblocking reaction organosilicon of four kinds of structures, through testing
Test, although the not isoplastic structure is slightly different to service performance, is attained by conductive effect of the invention, so this
Invention does not enumerate.
Claims (10)
1. heat cure no-solvent type organosilicon conductive adhesive, which is characterized in that based on parts by weight, including 10~40 parts of (methyl) third
The dimethyl silicone polymer of alkene acyloxyallcyl list sealing end, 50~80 parts of conductive powder bodies, 0.5-5 parts of free radical thermal initiators, 1~
10 parts of fumed silicas.
2. organosilicon conductive adhesive as described in claim 1, which is characterized in that (methyl) acryloxyalkyl list envelope
The structure of the dimethyl silicone polymer at end is as follows:
Wherein,
Wherein,
R1For H or methyl;
R2For CH2Or CH2CH2CH2;
R3For methyl, methoxyl group is or, ethyoxyl or isopropoxy;
R4For methyl, methoxyl group is or, ethyoxyl or isopropoxy;
The integer that n is 200~2000.
3. organosilicon conductive adhesive as described in claim 1, which is characterized in that the conductive powder body includes silver powder, wicker copper
Powder, nickel powder, carbon dust.
4. organosilicon conductive adhesive as described in claim 1, which is characterized in that the free radical thermal initiator includes azo
And organic peroxide.
5. organosilicon conductive adhesive as claimed in claim 4, which is characterized in that azo is AIBN or AIBME, organic peroxy
Object is lauroyl peroxide, benzoyl peroxide or peroxidized t-butyl perbenzoate.
6. organosilicon conductive adhesive as described in claim 1, which is characterized in that the fumed silica is dredged for AEROSIL
Aqueous silica R972.
7. monoblocking reaction organosilicon, which is characterized in that its structure is as follows:
Wherein,
R1For H or methyl;
R2For CH2Or CH2CH2CH2;
R3For methyl, methoxyl group is or, ethyoxyl or isopropoxy;
R4For methyl, methoxyl group is or, ethyoxyl or isopropoxy;
The integer that n is 200~2000.
8. the preparation method of monoblocking reaction organosilicon, which is characterized in that the steps include: containing (methyl) acryloxy
1.0~10 parts by weight of silane coupling agent and 100 parts by weight of hydroxy silicon oil issue under the action of catalysts in 80 ± 5 DEG C
Raw reaction, addition 1.0~10 parts by weight of hexamethyldisilazane remove the remaining hydroxyl of the other end after reaching certain viscosity, obtain
To the monoblocking reaction organosilicon.
9. method according to claim 8, which is characterized in that addition hexamethyldisilazane is removed after reaching certain viscosity
The remaining hydroxyl of the other end, the certain viscosity are 1.2~1.8 times of hydroxy silicon oil viscosity.
10. method according to claim 8, which is characterized in that the structure of hydroxy silicon oil is as follows:
The integer that n is 80~800.
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CN111423588A (en) * | 2020-05-06 | 2020-07-17 | 上海腾烁电子材料有限公司 | Single-end-capped propionyloxy organic silicon resin, preparation method thereof, conductive adhesive containing organic silicon resin and preparation method thereof |
CN111423588B (en) * | 2020-05-06 | 2022-04-01 | 上海腾烁电子材料有限公司 | Single-end-capped propionyloxy organic silicon resin, preparation method thereof, conductive adhesive containing organic silicon resin and preparation method thereof |
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